Allylic Oxidations of Olefins to Enones

Weidmann, Verena; Maison, Wolfgang

doi:10.1055/s-0033-1338491

Cited by 72 publications

(12 citation statements)

References 193 publications

(257 reference statements)

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“…No other example of this type of reactivity has later been reported. However, ruthenium-catalyzed allylic oxidations of olefins to enones is a known transformation and various ruthenium reagents have been used [151]. For example, the use of ruthenium (III) chloride, in conjunction with tert -butyl hydroperoxide as stoichiometric oxidant, has been reported [151].…”

Section: Ruthenium Tetroxide Chemistrymentioning

confidence: 99%

Ruthenium Tetroxide and Perruthenate Chemistry. Recent Advances and Related Transformations Mediated by Other Transition Metal Oxo-species

Piccialli

2014

Molecules

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Abstract:In the last years ruthenium tetroxide is increasingly being used in organic synthesis. Thanks to the fine tuning of the reaction conditions, including pH control of the medium and the use of a wider range of co-oxidants, this species has proven to be a reagent able to catalyse useful synthetic transformations which are either a valuable alternative to established methods or even, in some cases, the method of choice. Protocols for oxidation of hydrocarbons, oxidative cleavage of C-C double bonds, even stopping the process at the aldehyde stage, oxidative cleavage of terminal and internal alkynes, oxidation of alcohols to carboxylic acids, dihydroxylation of alkenes, oxidative degradation of phenyl and other heteroaromatic nuclei, oxidative cyclization of dienes, have now reached a good level of improvement and are more and more included into complex synthetic sequences. The perruthenate ion is a ruthenium (VII) oxo-species. Since its introduction in the mid-eighties, tetrapropylammonium perruthenate (TPAP) has reached a great popularity among organic chemists and it is mostly employed in catalytic amounts in conjunction with N-methylmorpholine N-oxide (NMO) for the mild oxidation of primary and secondary alcohols to carbonyl compounds. Its use in the oxidation of other functionalities is known and recently, its utility in new synthetic transformations has been demonstrated. New processes, synthetic applications, theoretical studies and unusual transformations, published in the last eight years (2006)(2007)(2008)(2009)(2010)(2011)(2012)(2013), in the chemistry of these two oxo-species, will be covered in this review with the aim of offering a clear picture of their reactivity. When appropriate, related oxidative transformations mediated by other metal oxo-species will be presented to highlight similarities and differences. An historical overview of some aspects of the ruthenium tetroxide chemistry will be presented as well.

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Section: Ruthenium Tetroxide Chemistrymentioning

confidence: 99%

Ruthenium Tetroxide and Perruthenate Chemistry. Recent Advances and Related Transformations Mediated by Other Transition Metal Oxo-species

Piccialli

2014

Molecules

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“…After 24 h of reaction, the was concentrated by vacuum distillation. The resulting crude residue was purified via column chromatographyon silica gel (petroleum ether/EtOAc, V∶V＝ 4∶1) to afford the intermediate with TEMPO (8). The desired AMP product was not observed and the intermediate with TEMPO (8) could be detected by 1 The deuteration of EMP was performed in a schlenk tube (50 mL) equipped with a magnetic stirrer.…”

Section: General Procedures For Oxidation Of Empmentioning

confidence: 99%

A Green and Scalable Cobalt(II)-Catalyzed Oxidation of 2-Ethyl-3-methylpyrazine

Chen¹,

Wang²,

Yu³

et al. 2020

Chin. J. Org. Chem.

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“…1 Among these reactions, allylic C−H oxidation to enone has received extraordinary attention due to the widespread existence of alkene substrates and the great importance of the resulting products. 2 For example, versatile naturally occurring compounds such as steroids and terpenoids contain double bond functionality, and the corresponding allylic C−H oxidized products are of significant economic and biological interest which can be used for drugs, dietary supplements, and flavor molecules (Scheme 1, A). 3 Conventional allylic C−H bond oxidation to enone relies on stoichiometric oxidants, such as chromium(VI) oxide and selenium dioxide (Scheme 1, B).…”

Section: ■ Introductionmentioning

confidence: 99%

Sustainable Aerobic Allylic C–H Bond Oxidation with Heterogeneous Iron Catalyst

Jiang,

Chen,

Chen

et al. 2024

J. Am. Chem. Soc.

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Emerging techniques are revolutionizing the realm of chemical synthesis by introducing new avenues for C−H bond functionalization, which have been exploited for the synthesis of pharmaceuticals, natural compounds, and functional materials. Allylic C−H bond oxidation of alkenes serves as possibly the most employed C−H bond functionalization reaction. However, sustainable and selective approaches remain scarce, and the majority of the existing conditions still hinge on hazardous oxidants or costly metal catalysts. In this context, we introduce a heterogeneous iron catalyst that addresses the above-mentioned concerns by showcasing the aerobic oxidation of steroids, terpenes, and simple olefins to the corresponding enone products. This novel method provides a powerful tool for the arsenal of allylic C−H bond oxidation while minimizing the environmental concerns.

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Allylic Oxidations of Olefins to Enones

Cited by 72 publications

References 193 publications

Ruthenium Tetroxide and Perruthenate Chemistry. Recent Advances and Related Transformations Mediated by Other Transition Metal Oxo-species

Ruthenium Tetroxide and Perruthenate Chemistry. Recent Advances and Related Transformations Mediated by Other Transition Metal Oxo-species

A Green and Scalable Cobalt(II)-Catalyzed Oxidation of 2-Ethyl-3-methylpyrazine

Sustainable Aerobic Allylic C–H Bond Oxidation with Heterogeneous Iron Catalyst

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